This invention relates to a process for the production of optically active 2-hydroxy-4-phenyl-3-butenoic acid. More particularly, it relates to a process for the production of optically active 2-hydroxy-4-phenyl-3-butenoic acid which comprises treating 2-oxo-4-phenyl-3-butenoic acid with an optionally treated microorganism capable of asymmetrically reducing the 2-oxo-4-phenyl-3-butenoic acid into (R)-2-hydroxy-4-phenyl-3-butenoic acid or (S)-2-hydroxy-4-phenyl-3-butenoic acid and collecting the (R)-2-hydroxy-4-phenyl-3-butenoic acid or (S)-2-hydroxy-4-phenyl-3-butenoic acid thus formed.
Optically active 2-hydroxy-4-phenyl-3-butenoic acid is an important intermediate in the production of various drugs, optically active and physiologically active substances and derivatives thereof.
Further, optically active 2-hydroxy-4-phenylbutyric acid, which is an important intermediate in the production of drugs such as ACE inhibitors, can be readily obtained by bringing optically active 2-hydroxy-4-phenyl-3-butenoic acid into contact with a hydrogenation catalyst such as palladium in a hydrogen atmosphere.
Known methods for the production of optically active 2-hydroxy-4-phenyl-3-butenoic acid include one which comprises treating a racemic mixture of said acid with bornylamine to thereby form diastereomers and then optically resolving the same [cf. Chem. Ber., 89, 671-677 (1956)] and another one comprising optical resolution through liquid chromatography with the use of a packing comprising a carrier containing a metal salt of an optically active amino acid bound thereto (cf. Japanese Patent Laid-Open No. 87640/1986). However, the former method requires a complicated procedure, which makes it undesirable from the industrial viewpoint. On the other hand, the latter method is disadvantageous from the economic viewpoint. Thus it has been demanded to develop a simple and economical method for producing optically active 2-hydroxy-4-phenyl-3-butenoic acid. In addition, there has been known no process for the production of optically active 2-hydroxy-4-phenyl-3-butenoic acid from 2-oxo-4-phenyl-3-butenoic acid by using a microorganism capable of asymmetrically reducing the 2-oxo-4-phenyl-3-butenoic acid.